Anna Karina

All kohl-rimmed cat eyes and wispy bangs, the New Wave siren and Jean-Luc Godard’s proto muse enchants generation after generation of film buffs. But cineastes aren’t the only ones to fall under Karina’s spell. She’s also one of the fashion industry’s most enduring inspirations, with everyone from Anna Sui to Jason Wu tapping into her singular style. Fun fact: Coco Chanel discovered Karina (a.k.a. Hanne Karin Blarke Bayer) and advised the then teenage model to change her name to something with a bit more je ne sais quoi.

Charlotte Rampling

Her famous green eyes sparkling with both cool reserve and fierce intelligence, it’s easy to understand why Rampling has often been called the thinking man’s sex symbol. And her choice of meaty roles, from The Swimming Pool to the controversial S&M thriller, The Night Porter, certainly gives credence to this claim. Woody Allen once said his ideal dinner companions are Charlotte Rampling and Franz Kafka. Perfect. We’ll bring the Chardonnay.

Patti Boyd

What do George Harrison’s “Something in the Way She Moves” and Eric Clapton’s “Wonderful Tonight” have in common? Both were written about Boyd. The British model met Harrison on the set of A Hard Day’s Night and the pair promptly wed. However, it wasn’t long before the duo acquired a third wheel in the form of a besotted Clapton who wasn’t shy about wooing—and eventually winning—his best mate’s wife.

Priscilla Presley

Have mercy! Graceland’s Lady of the Manor catered to her husband’s over-the-top tastes with a labor-intensive beauty regime that included false eyelashes, a stiff bouffant hairdo, and no shortage of eyeliner. After the couple separated, Presley toned down her makeup to let her considerable natural beauty shine through. Either way, she’s a major fashion muse (Christopher Kane cited her as an influence for his F/W 10 collection).

Winona Ryder

Ready for a mind melt? Reality Bites turns 20 this January. We know, we know. It seems like just yesterday that a Ryder was bewitching us on the big screen with her doe-eyed sex appeal and thrift store togs. We can also credit the Gen X leading lady for pioneering the slacker-chic look ­—torn boyfriend jeans, moto jackets—better known today as “model off-duty.”

Lisa Bonet

Bonet accomplished the impossible when she got notorious ladies man, Lenny Kravitz, to the altar. Of course, with her sensual features and free-spirited bonhomie, it’s easy to see why Kravitz put a ring on it. Alas, the union of the rock god and The Cosby Show actress didn’t last. But apart or together, the two are still dread sexy (sorry, had to).

Anjelica Huston

Together with partner, Jack Nicholson, Huston presided over 1970’s Hollywood with her aristocratic glamour and high fashion pedigree (she spent her late teens modeling for the likes of David Bailey and Bob Richardson). With her prominent nose, alabaster complexion, and lithe physique, her beauty was more compelling than conventional—a fact that makes us worship her that much more.

Edie Sedgwick

“It's not that I'm rebelling,” explained the Warhol muse of her wild child antics. “It's that I'm just trying to find another way.” Sedgewick similarly thought out of the box when it came to her eccentric signature look: heavy false eyelashes, chandelier earrings, and a silver pixie cut which mimicked Warhol’s.

Emmylou Harris

The godmother of alt country has collaborated with practically every influential musician in business, from Gram Parsons to Bob Dylan to Neil Young, but it’s her standalone talent that earns her a spot on this list. We also give a tip of the hat to her folk western style, which makes embroidered denim look cool.

Penelope Tree

A 16-year-old Tree’s arrival at Truman Capote’s famed Black and White Ball sparked a fury of “who’s that girl” inquiries and, just like that, a supermodel was born. She decamped to London, rubbed shoulders with famous actors and musicians, and became an emblem of the Swinging Sixties scene. Asked to describe Tree in three words, John Lennon reportedly exclaimed: “Hot, Hot, Hot, Smart, Smart, Smart!”

Grace Jones

No fashion education is complete without a course in Grace Jones Fabulousness. The glamazonian singer ruled the disco circuit with her androgynous good looks and fierce fashion. She rocked a flat top a good decade before anyone heard of Kid ‘n Play and is still inspiring the industry (the hair at Chanel’s Fall 13 Haute Couture show was influenced by said signature ‘do). Rumor has it she’s now at work on a memoir. Yes, please.

Sofia Coppola

Like a fine (Coppola) wine, the 42 year-old director’s fashion sense only gets better with age. These days, the Paris transplant favors an understated luxe look (crisp white shirts, ankle-skimming black trousers) with the occasional burst of insouciant glamour, like the metallic Marc Jacobs pajama set she wore to this year’s Met Ball.

Kate Moss

The fashion industry’s most enduring muse has worn many hats in the course of her career, from heroin-chic poster child to party-girl jetsetter to sophisticated clotheshorse par excellence. Her next move? Celebrating her 40th in—appropriately enough—her birthday suit with a nude spread in the January issue of Playboy. We’d expect nothing less from the catwalk’s reigning Queen of Cool.

Cher

Long before the sheer Bob Mackie bodysuits and feathered headdresses, Cher kept it simple(er) with a mod vibe that played up her killer cheekbones and swingy curtain of ebony hair that would bring Vidal Sassoon to his knees. The “If I Could Turn Back Time” singer has inspired scores of designers over the years, including Tom Ford who designed an entire Cher-inspired collection for Gucci in the late ‘90s.

Frida Kahlo

Never has a unibrow looked so chic. The Mexican artist’s memorable look (flower-festooned updo, colorful shawls, gold jewelry) and uncompromising persona has inspired decades of feminists and fashionistas (Kenzo, Riccardo Tisci) alike. Most recently, Rebecca Minkoff sent models down the runway of her S/S 14 show in crocheted pencil skirts that took their cues from Kahlo’s brand of Latin bohemianism.

Lee Miller

The Vassar–educated beauty and Vogue cover girl (discovered by Mr. Nast, yes of Conde Nast fame, himself) eventually made her way to Paris where she became Man Ray’s muse and a noted Surrealist artist in her own right. She shot a catalogue of lush images ranging from street scenes to nudes and —in collaboration Ray—rediscovered the photographic technique of solarisation. Those interested in learning more about Miller’s extraordinary life should check out Carolyn Burke’s seminal biography.

Nancy Sinatra

The bombshell daughter of Ol’ Blue Eyes inspired a legion of imitators with her signature ‘60s style: big hair, short skirts, and go-go boots —the latter of which was the subject of her # 1 hit single and the ultimate ode to footwear, “These Boots were Made for Walking.”

Patti Smith

Perhaps the cultiest of the cult icons, Smith’s rangy good looks and borrowed-from-the -(bad) boys fashion can be an acquired taste. But those susceptible to the charms of the original princess of punk fall hard and never quite recover, as Ann Demeulemeester whose long found a muse in Smith, can attest.

Tavi Gevinson

The Rookie Editor-in-Chief might be thinking about quitting fashion, but the fashion world clearly isn’t ready to quit her. The precocious tween style blogger who captured our hearts with her granny glasses and Rodarte obsession has blossomed into an impressive young lady/promising actress with, no surprises here, a sophisticated sartorial sense.

Yoko Ono

Did Yoko break up The Beatles? Ono she didn’t! Now that the obligatory pun’s out of the way, we can say with some certainty that The Fab Four were headed for splitsville without any help from Lennon’s lady love. On the other hand, Ono has had a plenty of influence in the fashion sphere with Proenza Schouler name-checking her as an influence for their F/W 12 presentation, Opening Ceremony tapping her to design a collection, and Chanel featuring her in its tome, The Little Black Jacket: Chanel’s Classic Revisited.